115890-53-4

Upstream product

• 67-56-1 methanol 
• 206126-49-0 (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester 
• 99027-88-0 N-(benzyloxycarbonyl)-2-oxa-3-azabicyclo<2.2.1>hept-5-ene 
• 115890-52-3 (2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine 
• 115890-44-3 (2S,3S,4R)-<1-(benzyloxycarbonyl)-2-(hydroxymethyl)-4-(1-hydroxy-1-methylethyl)>-3-pyrrolidineacetic acid lactone 
• 115890-51-2 (2S,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(2-hydroxy-ethyl)-4-isopropenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 115890-38-5 ((R)-2-Benzyloxy-1-formyl-ethyl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester 
• 115890-49-8 (2S,3S,4R)-1-(benzyloxycarbonyl)-2-<<(tert-butyldimethylsilyl)-oxy>methyl>-3-(2-hydroxyethyl)-4-(1-hydroxy-1-methylethyl)pyrrolidine 
• 1066877-98-2 (S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 302906-15-6 ((3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester 
• 302906-13-4 [(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enyl]-carbamic acid benzyl ester 
• 205675-73-6 Acetic acid (1S,4R)-4-benzyloxycarbonylamino-cyclopent-2-enyl ester 
• 205675-68-9 cis-4-carbobenzoxyamino-2-cyclopentenol 

Downstream Products

• 73903-33-0 (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid 
• 115890-52-3 (2S,3S,4S)-1-(benzyloxycarbonyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-isopropenylpyrrolidine 
• 487-79-6 (-)-kainic acid 

Relevant academic research and scientific papers

A concise route to (-)-kainic acid.

A concise route to (-)-kainic acid from enantiopure (+)-cis-4-carbobenzoxyamino-2-cyclopentenol has been devised by employing concurrent Chugaev syn-elimination and intramolecular ene reaction as the key step.

New enantioseleetive approach to the total synthesis of (-)-α-Kainic Acid

The total synthesis of (-)-α-Kainic Acid 1 has been accomplished using ethyl N-Boc-pyroglutamate 2 as starting material. The isopropenyl appendage was achieved from the elimination of the dimethylcarbinol introduced at C-4 via an aldol condensation of the lactam enolate of 2 and acetone. The acetate group at C-3 of the kainic acid structure was introduced via diethyl malonate Michael addition reaction to the 2,3-didehydroprolinate 8. This Michael addition reaction proceeds with complete stereocontrol over the newly generated stereogenic centres. Inversion of the configuration at C-3 in 9 through double bond formation followed by hydrogenation, neutral decarboxylation and further epimerization of the C-2 stereogenic centre in 12, gave rise to the desired natural product.

Enantioselective synthesis of (-)-kainic acid

Novel diastereoselectivity in the intramolecular Diels-Alder reaction of the heterodiene 18 has been observed. The structure of the cycloadduct was determined to be 20, possessing cis-5/6 ring juncture by converting it into (-)-kainic acid and kainic acid lactone.

A Concise Enantioselective Route to (-)-Kainic acid from (S)-2-(Benzyloxymethyl)oxirane

A concise enantioselective route to (-)-kainic acid (1) from (S)-2-(benzyloxymethyl)oxirane (2) has been established by enentio- and diastereo-selective intramolecular 1,3-dipolar cyclization.